Megan Casebier

Lead UX strategy and direction for Obie’s two-person design team—owning research, systems design, and product direction while the UI designer owns visual execution. Embedded on a 12+ person cross-functional product team spanning Product, Engineering, Underwriting, and Compliance. Promoted following leadership of a company-wide rebrand and expansion into new lines of business during acquisition.

• Designed and led UX architecture for Obie’s Agent Experience (AURA), expanding the business from a D2C-only model to a B2B2C platform enabling 1,300+ independent insurance agents to quote and bind policies. This line of business now represents ~90% of company revenue.
• Led UX strategy for Obie’s expansion into homeowners insurance—a 0→1 product built on a carrier-agnostic architecture supporting 3 package types (HO3/HO5/HO6) with seamless switching, shipped bind-ready on deadline.
• Redesigned the partner authorization system in 2.5 weeks using AI-assisted rapid prototyping—first working prototype delivered within hours, compressing a 6-week design cycle. Reframed the data model from restrictions to allowances, reducing database complexity by 99.7% (306 records per partner → 1).
• Built an interactive QA walkthrough using AI-assisted development to track 52 design-to-implementation discrepancies with severity coding, code fix suggestions, and resolution tracking. Engineering used it to resolve all 52 issues before launch—more UI work shipped pre-launch than any previous release.
• Redesigned the Agent Resource Hub using AI-assisted rapid prototyping, achieving full stakeholder alignment in a single day. Introduced a product-branching information architecture that scales to new insurance lines without restructuring.
• Established Obie’s design culture as a two-person team—created design reviews, hackathons, brown bag sessions, and cross-functional presentation practices.

Started at the front desk at Orangetheory Fitness; created a UX role during COVID to bring virtual workouts to members when studios closed. Simultaneously led digital transformation at Firebrand Sports, retaining ~75% of active members through a virtual platform. Transitioned into dedicated UX research and design roles at StrongArm and FleetOps.

• Drove 44% increase in weekly active users through generative research that reshaped product direction; achieved 38% 60-day retention rate, nearly double industry benchmarks (StrongArm).
• Redesigned core onboarding experience resulting in 70% increase in new user retention (FleetOps).
• Conducted ethnographic research across 5 client facilities, uncovering behavioral patterns that reframed core product assumptions (StrongArm).